DE3891468T1 - AETHYL ESTER OF 6-BROM-5-HYDROXY-4-DIMETHYLAMINOMETHYL-1-METHYL-2-PHENYLTHIOMETHYLINDOL-3-CARBONIC ACID OF MONOHYDRATE HYDROGEN CHLORIDE, METHOD FOR ITS PRODUCTION OF INTERMEDIATE CLEANING - Google Patents
AETHYL ESTER OF 6-BROM-5-HYDROXY-4-DIMETHYLAMINOMETHYL-1-METHYL-2-PHENYLTHIOMETHYLINDOL-3-CARBONIC ACID OF MONOHYDRATE HYDROGEN CHLORIDE, METHOD FOR ITS PRODUCTION OF INTERMEDIATE CLEANINGInfo
- Publication number
- DE3891468T1 DE3891468T1 DE883891468T DE3891468T DE3891468T1 DE 3891468 T1 DE3891468 T1 DE 3891468T1 DE 883891468 T DE883891468 T DE 883891468T DE 3891468 T DE3891468 T DE 3891468T DE 3891468 T1 DE3891468 T1 DE 3891468T1
- Authority
- DE
- Germany
- Prior art keywords
- phenylthiomethylindol
- brom
- dimethylaminomethyl
- hydroxy
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/SU1988/000272 WO1990008135A1 (en) | 1989-01-12 | 1989-01-12 | Ethyl ester 6-bromine-5-hydroxy-4-dimethyl-aminomethyl-1-methyl-2-phenylthiomethyl indole-3-carboxylic acid hydrochloride monohydrate, method of obtaining it and a pharmaceutical preparation of antiviral, interferon inducing and immunomodulating action based on it |
Publications (1)
Publication Number | Publication Date |
---|---|
DE3891468T1 true DE3891468T1 (en) | 1991-02-21 |
Family
ID=21617367
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE3891468A Expired - Fee Related DE3891468C2 (en) | 1989-01-12 | 1989-01-12 | Ethyl ester of 6-bromo-5-hydroxy-4-dimethylaminomethyl-1-methyl-2-phenylthiomethylindole-3-carboxylic acid monohydrate hydrochloride, process for its preparation and pharmaceutical preparation with antiviral, interferon-inducing and immunomodulating action on its basis |
DE883891468T Pending DE3891468T1 (en) | 1989-01-12 | 1989-01-12 | AETHYL ESTER OF 6-BROM-5-HYDROXY-4-DIMETHYLAMINOMETHYL-1-METHYL-2-PHENYLTHIOMETHYLINDOL-3-CARBONIC ACID OF MONOHYDRATE HYDROGEN CHLORIDE, METHOD FOR ITS PRODUCTION OF INTERMEDIATE CLEANING |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE3891468A Expired - Fee Related DE3891468C2 (en) | 1989-01-12 | 1989-01-12 | Ethyl ester of 6-bromo-5-hydroxy-4-dimethylaminomethyl-1-methyl-2-phenylthiomethylindole-3-carboxylic acid monohydrate hydrochloride, process for its preparation and pharmaceutical preparation with antiviral, interferon-inducing and immunomodulating action on its basis |
Country Status (10)
Country | Link |
---|---|
US (1) | US5198552A (en) |
BE (1) | BE1003341A4 (en) |
CH (1) | CH678726A5 (en) |
DE (2) | DE3891468C2 (en) |
DK (1) | DK15490A (en) |
FR (1) | FR2650504B1 (en) |
GB (1) | GB2234510B (en) |
NL (1) | NL9000265A (en) |
SE (1) | SE465462B (en) |
WO (1) | WO1990008135A1 (en) |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3891468C2 (en) * | 1989-01-12 | 1994-02-24 | Vni Skij Chimiko Farmacevtices | Ethyl ester of 6-bromo-5-hydroxy-4-dimethylaminomethyl-1-methyl-2-phenylthiomethylindole-3-carboxylic acid monohydrate hydrochloride, process for its preparation and pharmaceutical preparation with antiviral, interferon-inducing and immunomodulating action on its basis |
US5945425A (en) | 1994-04-29 | 1999-08-31 | G.D. Searle & Co. | Method of using (H+ /K+)ATPase inhibitors as antiviral agents |
CN100361975C (en) * | 2003-01-04 | 2008-01-16 | 沈阳药科大学 | Novel 5-hydroxy-3-carboxylate indoles derivant and method for preparing the same |
CN1560035A (en) | 2004-03-12 | 2005-01-05 | 沈阳药科大学 | 5-hydroxylic indole-3-carboxylic ester kind derivantion |
CN100519523C (en) * | 2004-03-12 | 2009-07-29 | 沈阳药科大学 | 5-hydroxyindole-3-carboxylate derivative and its use |
CN100364975C (en) * | 2005-04-26 | 2008-01-30 | 武汉大学 | Medication for anti virus of respiratory tract and application |
CN1316968C (en) * | 2005-09-30 | 2007-05-23 | 青岛大学 | Application of indole-2,3-diketone in preparing medication for antivirus or immunopotenfiator |
US8329689B2 (en) | 2006-05-23 | 2012-12-11 | Alexandre Vasilievich Ivachtchenko | Substituted indoles and a method for the production and use thereof |
CN101070319B (en) * | 2007-05-29 | 2012-04-18 | 沈阳中海生物技术开发有限公司 | Crystal state of anti-hepatitis-B-virus compound and its preparing method and use |
CN103189354A (en) | 2010-07-16 | 2013-07-03 | 格林代克斯联合股份公司 | Derivatives of 1,4-dihydropyridine possessing antiviral efficacy |
CN102786462B (en) * | 2011-05-18 | 2016-08-31 | 中国医学科学院药物研究所 | Arbidol hydrochloride crystal B-type and preparation method are applied with in medicine and health product |
CN102786461B (en) * | 2011-05-18 | 2016-08-31 | 中国医学科学院药物研究所 | Arbidol hydrochloride crystalline substance E type and preparation method are applied with in medicine and health product |
CN102351778A (en) * | 2011-08-17 | 2012-02-15 | 湖北华龙生物制药有限公司 | Preparation method of arbidol hydrochloride |
EP2578218A1 (en) | 2011-10-06 | 2013-04-10 | Grindeks, A Joint Stock Company | Antiviral efficacy of disodium 2,6-dimethyl-1,4-dihydropyridine-3,5-bis(carbonyloxyacetate) and its derivatives |
CN104193669B (en) * | 2014-08-01 | 2016-12-07 | 大连理工大学 | One class Abiduoer analog or its salt, its preparation method and application |
CN106083691B (en) * | 2016-08-22 | 2018-11-27 | 山东罗欣药业集团恒欣药业有限公司 | A kind of preparation method of arbidol HCl monohydrate |
WO2021209563A1 (en) | 2020-04-16 | 2021-10-21 | Som Innovation Biotech, S.A. | Compounds for use in the treatment of viral infections by respiratory syndrome-related coronavirus |
CN111533677A (en) * | 2020-05-13 | 2020-08-14 | 大连万福制药有限公司 | Method for synthesizing arbidol hydrochloride intermediate |
CN116003308B (en) * | 2022-12-27 | 2023-09-29 | 石家庄中硕制药有限公司 | Abidol crystallization process |
CN117586173A (en) * | 2023-11-29 | 2024-02-23 | 石家庄中硕制药有限公司 | Preparation method of arbidol |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4124702A (en) * | 1971-07-06 | 1978-11-07 | Merck & Co., Inc. | Polynucleotides active as inducers of interferon production in living animal cells |
US4215137A (en) * | 1978-06-26 | 1980-07-29 | Sterling Drug Inc. | Method of alleviating diseases by cell-mediated immune modulation |
US4619942A (en) * | 1982-04-08 | 1986-10-28 | University Of North Carolina | Inhibition of Respiratory Syncytial virus-induced cell fusion by amidino compounds |
US5079257A (en) * | 1986-04-17 | 1992-01-07 | Speckamp Willem N | Indoloquinone compounds |
WO1988005432A1 (en) * | 1987-01-23 | 1988-07-28 | Yoshitomi Pharmaceutical Industries, Ltd. | 5-hydroxyindole-3-carboxamide compound and medicinal use thereof |
JPS63188665A (en) * | 1987-01-30 | 1988-08-04 | Yoshitomi Pharmaceut Ind Ltd | 5-hydroxyindole-3-carboxylic acid ester compound |
DE3891468C2 (en) * | 1989-01-12 | 1994-02-24 | Vni Skij Chimiko Farmacevtices | Ethyl ester of 6-bromo-5-hydroxy-4-dimethylaminomethyl-1-methyl-2-phenylthiomethylindole-3-carboxylic acid monohydrate hydrochloride, process for its preparation and pharmaceutical preparation with antiviral, interferon-inducing and immunomodulating action on its basis |
-
1989
- 1989-01-12 DE DE3891468A patent/DE3891468C2/en not_active Expired - Fee Related
- 1989-01-12 US US07/576,444 patent/US5198552A/en not_active Expired - Fee Related
- 1989-01-12 WO PCT/SU1988/000272 patent/WO1990008135A1/en active Application Filing
- 1989-01-12 DE DE883891468T patent/DE3891468T1/en active Pending
- 1989-01-12 CH CH3071/90A patent/CH678726A5/de not_active IP Right Cessation
- 1989-08-04 FR FR8910558A patent/FR2650504B1/en not_active Expired - Fee Related
-
1990
- 1990-01-19 DK DK015490A patent/DK15490A/en not_active Application Discontinuation
- 1990-01-23 BE BE9000076A patent/BE1003341A4/en not_active IP Right Cessation
- 1990-01-26 SE SE9000282A patent/SE465462B/en unknown
- 1990-02-02 NL NL9000265A patent/NL9000265A/en not_active Application Discontinuation
- 1990-09-11 GB GB9020370A patent/GB2234510B/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
DK15490A (en) | 1991-07-20 |
BE1003341A4 (en) | 1992-03-03 |
DE3891468C2 (en) | 1994-02-24 |
GB9020370D0 (en) | 1990-11-21 |
FR2650504A1 (en) | 1991-02-08 |
GB2234510A (en) | 1991-02-06 |
DK15490D0 (en) | 1990-01-19 |
NL9000265A (en) | 1991-09-02 |
FR2650504B1 (en) | 1993-12-24 |
SE465462B (en) | 1991-09-16 |
SE9000282D0 (en) | 1990-01-26 |
CH678726A5 (en) | 1991-10-31 |
WO1990008135A1 (en) | 1990-07-26 |
GB2234510B (en) | 1992-03-25 |
US5198552A (en) | 1993-03-30 |
SE9000282L (en) | 1991-07-27 |
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